(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 220569-29-9
• Molecular Formula: C₂₅H₂₉NO₄
• Molecular Weight: 407.51
• Mol file: 220569-29-9.mol

Synonyms:(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

There total 1 articles about (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 77.0%

allyl bromide (106-95-6) + (2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (191980-50-4) → (2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (220569-29-9)

Guidance literature:

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

allyl bromide; In tetrahydrofuran; toluene; at -78 - 25 ℃; for 16h;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield: 95.0%

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (220569-29-9) → (2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (220569-30-2)

Guidance literature:

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 25 ℃;

DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

(2S,4S)-4-allyl-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester (220569-29-9) → (2S,3S)-N-[3-benzyl-1-(2-hydroxyl-1-methyl-ethyl)-2-oxo-pyrrolidin-3-yl]-methane-sulfonamide (220569-48-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

1.2: 95 percent / Me₂S / CH₂Cl₂; methanol / -78 - 25 °C

2.1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

3.1: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

4.1: 90 percent / hydrogen / Pd/C / ethanol / 17 h

5.1: 61 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

6.1: 65 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / -5 - 25 °C

With pyridine; dmap; sodium tetrahydroborate; 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1.1: ozonolysis / 1.2: Reduction / 2.1: Alkylation / 3.1: Cyclization / 4.1: Hydrogenolysis / 5.1: Substitution / 6.1: Reduction;

DOI:10.1016/S0968-0896(98)80022-9

upstream raw materials:

allyl bromide

(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

(2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

(2S,3S)-N-[3-benzyl-1-(2-hydroxyl-1-methyl-ethyl)-2-oxo-pyrrolidin-3-yl]-methane-sulfonamide

(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester